Acetic Acid → 4-Acetoxy-2-fluorobenzoic acid

HRID 1739600Notes

Reaction equation

HRID 1739600 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([F:11])[CH:3]=1.[C:12](O)(=[O:14])[CH3:13]>S(=O)(=O)(O)O.O>[C:12]([O:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([F:11])[CH:3]=1)(=[O:14])[CH3:13]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 27833982-Fluoro-4-hydroxybenzoic Acid

Product 1

HCID 227214164-Acetoxy-2-fluorobenzoic acid

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

6 Grams of 4-hydroxy-2-fluorobenzoic acid and 8.2 g of anhydrous acetic acid were placed in a two-necked flask, and mixed. While the mixture was cooled with water, 5 drops of sulfuric acid were added. After heat generation was terminated, the mixture was heated at 80° C. for 30 minutes. Then, the reaction mixture was poured into cold water, and a precipitated crystal was recovered by filtration. The crystal was vacuum-dried, and used in the next step. The yield of the crystal was 4.8 g.

Workup

  1. additionmixed
  2. additionwere added
  3. temperatureAfter heat generation
  4. customwas terminated
  5. additionThen, the reaction mixture was poured into cold water
  6. filtrationa precipitated crystal was recovered by filtration
  7. customThe crystal was vacuum-dried

Sources & evidence

ORD record
ord-bcc113bee0bc451ea408105ab3dc2b07
Source dataset
uspto-grants-1999_10
Patent number
US05968413

Reaction notes

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